My Trans Girlfriend and My Sister

Warning: This story involves sex with a trans woman and my sister. If either transgender stories or incest are not to your liking; unfortunately, this story will not be for you. I have given my trans girlfriend in the story feminine pronouns (eg. "She" and "her") For the sake of creative convenience.

I started dating Michelle about 3 months ago. She is my transgender girlfriend. I never had any gay thoughts or even considered being with someone who had a dick; but this was one of those things that just happened. I met her at a bar one night and found her attractive straight away. She was the spitting image of Candace Owens. She even spoke like her. I actually asked Michelle if she was the famous YouTube star, to which she corrected me and told me that she got asked that a lot. I was conversing with what had to be the closest thing I'd ever seen to a full-on doppelganger. As the night when on, the bar staff had moved a load of tables so that there was now a dancefloor. With a few drinks in both of us, I asked Michelle if she wanted to dance. As we danced to some generic dance beat, I looked into her eyes and saw her infectious smile. I thinking to myself that I was dancing with Candace Owens. I always found her hot after I discovered her channel. I had jacked off to her videos time and time again; particularly those where her hair is down, climax at the thought of covering her face with my cum.

Michelle turned around and started grinding on me. My dick immediately got hard at the contact with her cute butt. Her reaction to my erection was to push deeper into my crotch. My hands reached her legs as I caressed her inner thighs, which were hugged by her tight jeans. She turned back around so now my hands were on her lower back. That delightful grin returned and I couldn't resist. I leaned in to kiss her and she reciprocated. We made out on the dancefloor for several minutes. My hands pinched her ass as out tongues played with more passionate kissing.

I asked her if she wanted to get an uber but she told me she couldn't leave as she was waiting for her brother to finish his shift at the bar. She was staying with him until she could move into her own place. Instead, she took me by the hand and led me to the male bathrooms.

"Are you sure!" I asked, pointing at the sign on the door. She told me not to worry about it and we found a cubicle. The kissing resumed as Michelle undid my belt. She got on her knees and took out my cock before putting my 10-inch cock in her mouth. It was unbelievable. It didn't take long for her to work out the most sensitive part of my shaft; just below the head. She ran her tongue along the underside of my penis and sucked on my balls. It's a good thing the bar wasn't busy; at least the bathrooms weren't. Even if they were, I wouldn't be able to contain my loud moans from the sexual pleasure this blowjob was giving me. In my head, I was getting a blowjob from Candace Owens. As this was a recurring fantasy for me, I told Michelle I wanted to cum on her face.

"I'm not cool with that, but I'll swallow your load. How 'bout that?" That delicious smile reappeared as she looked up at me with my dick still in her hand, giving my head a series of pecks. I wasn't far from climaxing after a minute of Michelle fully sucking my dick. I told her I was gonna cum and began thrusting into her mouth. With one hand behind her head and the other on the wall. With one long groan I blew my load into her mouth. She allowed my river of cum to flow down her throat as she swallowed what was left from my balls.

"Hmmmmm. That tastes so good." She told me as cleaned up my dick with kisses and licks, making sure she got every last drop.

"Wow, Michelle." I exhaled, looking down at the face of the Candace Owens lookalike that had just blown me. "That was amazing."

"Yeah, I know. I'm fucking hard now. You can do me!"

"You're hard!!?" I reacted in shock. "Wait, what? You're a guy!!??"

"No I'm not a guy." She snapped. "I'm trans. Identify as a woman!"

"Alright, whatever...Look I'm not sure if I'm comfortable with this. I didn't realize you had a dick!" I was starting to panic.

"Oh, that's fair!" She replied sarcastically. "I suck your dick but you don't suck mine? You've clearly had the hots for me all night. You sure as hell didn't have any issues grinding on my ass!"

"I know." I confessed. "I think you're beautiful and I really like you. I think we have a personal connection and we have a lot in common, but I've never been in a sexual relationship that involved another dick but mine. I do wanna see you again. I just need to think some things over."

She told me that she understood my feelings. She appreciated the fact that I wasn't rude about it and was flattered that I still wanted to see her. She told me that a similar experience had happened about a year ago but the guy tried to be violent towards her once he realized that she wasn't all female. She told me that she was a blackbelt in jujitsu and perfectly capable of defending herself physically. We exchanged numbers and she walked me to the bus stop outside the bar. Michelle told me she looked forward to seeing me again and that we could take things slow. We kissed again before the bus arrived. She joked about me tasting my own cum before turning to walk back to the bar.

"Well guy or trans or whatever, that ass is fucking hot." I thought to myself before boarding the bus to go home.

From that point on we met 2 or 3 times a week as our attraction to each other grew. So far, our meetings were not sexual. Instead we would have dinner, go for walks in the park and watch movies. Primarily though, we would mostly just spend hours talking and making each other laugh as out bond and connection grew.

I decided I was comfortable with us kissing so we would make out more often each time we met, especially when she came over to my place. One Saturday though; about a month into our relationship, we were snuggling on the couch watching a documentary. I had my hand on her ass while her head rested on my chest. She noticed the bulge grow in my pants and started rubbing my crotch while we kissed. It must have been the booze that led to me to tell Michelle that we should move to the bedroom.

"Okay Craig, we're in your bedroom. What do you wanna do?" She asked, winking.

"I want you to wet my bit with your mouth before I fuck your sexy ass!"

Michelle reacted with excitement while unzipping my pants and sucking on my dick. I leaned my head back with pleasure as this blowjob was better than the one in the bar.

"Okay, you seem ready." She got up on the bed on all fours and lifted up her skirt as I pulled down her panties and slowly jammed the head of my big dick into her tiny asshole. I had never had anal sex before but as I slowly forced more of myself into her, I wondered why I had missed out on such an amazing sensation all these years. She pushed back into me as I fucked her ass. I started to groan with arousal.

"Oh Craig, your cock feels so good. Keep fucking me baby!"

"Oh, fuck your ass is amazing!" I uttered while pumping her butt in ecstasy. Both of us breathed more heavily as I drilled deeper into her ass. Our moans got louder and more frequent. I put all my energy into penetrating her tight asshole. Our rhythm was perfectly in sync as I grew closer to cumming. This was a level of passionate love making I've never experienced before.

"I'm gonna come in your ass Michelle!" I uttered into her ear.

"Do it baby. Fill my ass with your cum!" She turned to kiss me. Our lips locked as I unleashed a month's worth of backed up semen into the depths of her ass. We both screamed with sexual pleasure as I drained my balls into her rectum. Exhausted, we collapsed onto the bed. I lay on top of her with my dick slowly softening in her ass; the last drops of cum leaving my dick. We just lay there, breathing heavily before sharing a deep kiss. I told her that experience was amazing and that I thought I loved her. I'd never felt this way about anyone before, to which she replied with the same sentiment. I told her we should go to sleep. My sister, who also had a room in this apartment, was returning from her backpacking trip and I needed to clean up before she got home. Michelle told me she loved me and we kissed again for another minute. I was totally wiped out from that trance and passed out almost immediately.

I woke up about an hour later to feel something pushing into the crack of my ass. I turned round to see Michelle was humping her hard dick against me. I asked her to stop because I was tired and didn't have the energy for more sex.

"Oh, come on baby." She whined. I've let you cum in my mouth AND my ass. I haven't had any release in weeks."

"I'm sorry, babe. You'll just have to wait."

"Just touch it." She begged. "Here, I'll grab your dick and you grab mine." She placed my hand on her hard dick and reached into my boxers with her other hand, massaging my dick, which started to grow from the contact. "I'm left-handed, so it'll just be like we're both just jerking ourselves off." Her technique was so good that I soon found myself too aroused to care and moved my hand up and down Michelle's dick. We turned to kiss while our dicks grew harder from each other's jerking. I pumped that dick like it was my own and the movements grew harder and faster as we both got turned on. As we both got close to climax, our lips locked hard and we both came all over the underside of my bed covers. Each of us jacking and cumming more to the sound of the other's orgasm. She moaned long and loud as her ejaculation was greater than mine. She came about as much as I had previously when I'd been pumping her ass. She thanked me and kissed me again before we fell asleep in the spooning position.

When I awoke, I looked down to see my hard dick was lodged in between Michelle's ass cheeks. Feeling horny, I couldn't stop myself from rubbing my cock up and down her crack. I could feel her cute butt clench on my dick. She wasn't asleep for long. She realized what was happening and told me to snap out of it.

"Hey, Craig. Not now. We got clean up, remember?"

"Yeah, you're right. Lets' take a shower." We both go into the bathroom and stepped into the shower together. I wasn't the only one with morning wood. She had a big black dick that was only about an inch smaller than mine. I never thought of myself as somebody who would be erect around a big black dick and balls, but Michelle had shaved her entire nether regions. It didn't look too bad after all.

"Wow, someone likes my dick!" She remarked, giggling at the sight of catching me looking at her erect penis, which she was flexing at me. I looked up to that irresistible smile and leaned in to kiss her. As we made out on the shower, my boner grew to the point where the heads of our dicks made contact. I pulled from the kiss to look down at the contact.

"Just go with it. Michelle whispered, sensing my discomfort, and we went back to French kissing. She put her arm around me and I grabbed her ass, pulling our bodies closer. I became so turned on that I started to jerk off while we kissed. Realizing what I was doing, Michelle did the same. We just pumping our dicks in arousal at each other. She bit my bottom lip as she came all over my balls and inner thighs. Her orgasm stimulated me more as I jerked harder and faster with my eyes on the Candace Owens face that I'd gotten so attracted to. Michelle kneeled down to lick up all the cum off my legs and balls. I moved my hand down my shaft to allow the head into her mouth. With her lips around the end of my member I pumped the rest of my dick with my hand.

"Lemme cum on your face, please!" I pleaded.

"Okay, baby. Go ahead. Cum on my face!" She smiled while giving sloppy wet kisses to my head and the underside of my shaft. My dick ran along her face as she kept working on my dick with those moist lips.

"Here is comes, baby!" I cried, looking at my girlfriend's face. Her eyes were closed as she continued to kiss my dick. I moaned intently as my head erupted all lover Michelle's forehead. She kept her eyes tightly shut as cum covered her face. Michelle didn't take her lips off the underside of my shaft as the last shots of semen left my dick. Once I was finished, Michelle stuck her face under the shower to clean the cum off her face.

"Not a bad way to start the day." She laughed as we cleaned ourselves up, resisting the temptation to go again. I appreciated Michelle's offer to help me get the place spotless as it would take less time, but I knew that we didn't have all day.

We both got dressed into fresh clothes; Michelle wore the same skirt and top from the previous night. As we cleaned the communal areas of the apartment, I got a voicemail on my cell phone.

"Hey, Bro. It's Kim. I just landed at the airport. I'll be home at around 3 o'clock. Look forward to seeing you!" Looked at the clock to see that it was almost 1pm.

"Okay, so my Sister is gonna be here in 2 hours." I told Michelle.

"Great! So, does that leave us enough time for you to finally give me a blowjob?" She asked.

It was hard for me to say no to that breathtaking smile but I still wasn't ready to suck a dick; besides, I knew that Kimberly would come down on me hard if she came back to a messy house after being on the other side of the world. Michelle accepted my reluctance and didn't make a fuss about it. We worked hard to clean up after my laziness and procrastination into getting the work done earlier. The apartment was spotless with about twenty minutes to spare before my sister would arrive. I was bent over, picking the last of the trash bags to be taken about the house.

"Hmmmmm. You have such a cute butt, Craig." Michelle told me. She was clearly horny. She had come up behind and pushed her boner into the crack of my ass. I told her to back off.

"But I'm so hard from you, baby. I need my dick to be enclosed in your lips." Turning round and bending her pretty ass towards me. "Isn't there some way I can convince you?" She asked sexily wiggling her butt at me. I firmly told her that we weren't gonna fool around in case my sister walked in on us. I hadn't told her I was dating anyone, let alone a trans woman. It seemed to be just in time as I heard the door open.

"Hello?" I heard a cry. I moved downstairs to the front door to greet my sister. "Hey little bro!" She cried as she ran into my arms, the two of us sharing a loving hug. My sister was wearing a low-cut sleeves top and tight white shorts. The backpacking had been good to her. She had lost loads of weight but she looked great. Her beach blonde hair was complimented by her natural bronze tanned skin. Her legs were thick but athletic and her stomach was flat, which made her big tits jump out in a way I'd never appreciated. I told her that she looked amazing and she clearly enjoyed my words. She was feeling that way about herself. She always used to be a heavyset girl with no real shape, but now she was voluptuous as hell. Michelle must have heard our conversation because I heard her coming don the stairs.

"Wow! You look great!" Michelle said to my sister as she arrived at the front od the stairs. "I love your hair and the sun has been good to you, huh?"

"Oh, I didn't realize you had company." Kimberly was feeling a lil awkward looking from Michelle back to me as she said that."

"Kim, this is my friend Michelle." They smiled and shook hands. My sister commented on Michelle's smile. It wasn't just me you had a liking for it. I told them both that I had to get rid of these last few trash bags and asked Kim if she wanted me to get anything from the store.

"Alcohol!" Kim blurted out whilst looking at my girlfriend, who Kim appeared to seriously doubt was born a girl. I asked what kind and she said vodka. I told her we had some fruit juices that could mix with and that I'd pick up some ice.

I was as the store for longer than I'd hoped. There was a line of people and the guy at the front was so drunk he wasn't able to communicate what he wanted. It seemed like he didn't have enough money. Eventually the teller just gave him a pack of cigarettes so that he's be gone. I'd been away from the apartment for about 25 minutes. I walked up the stairs of my building to hear what I thought were screams outside my door. I quickly unlocked the door and burst inside. I followed the noise and arrived in the living room to be greeted by a sight that was so alarming, I dropped all the bags that I was holding, smashing both vodka bottles in the process. Glass and vodka were all over the floor. I couldn't believe what I was seeing or hearing. Michelle was sat on the couch with her head leant back, moaning from sexual pleasure, while in front of her was my blonde sister on her knees bent over with her big ass in white shorts pointing at me. Kimberly was sucking my girlfriend's cock.

"What the fuck is going on here!!?" I bellowed, horrified by what was in front of me.

"I'm sorry, baby" Michelle replied "But I really wanted a blowjob and your sister is hot and she's so good at giving head." Placing her had onto my sister's head and begging her not to stop.

"Michelle, you're cheating on me with my sister!!?? How could you!!?" I felt so betrayed.

"It's not cheating if you get involved, baby." She responded.

"Get involved? How am I supposed to get involved!??" I cried.

"You could come over here and join you sister" Michelle answered.

"What? Are you crazy!??" I've sucked a dick before! What makes you think I'm gonna share my first experience with my sister!?? And Kim. What the hell!?? What do you have to say for yourself!???" My sister took Michelle's dick out of her mouth but didn't look at me to respond, her eyes glued to the big black dick she was holding.

"I'm sorry, lil bro. I didn't know you two were fucking. I didn't think you were in to chicks with dicks. I think it's fucking hot. It's the best of both worlds!" I recoiled with revulsion when she said that.

"Come on baby, don't you think your sister's hot?" Michelle asked me; standing up off the couch and leaning over my sister to place her hands on Kimberly's ass. "Don't you like your sister's big booty?" She was jiggling my sister's fleshy ass in front of me, trying to entice me. Kimberley was running her tongue along Michelle's hard cock.

"Kimberly! Aren't you grossed out!?? Why don't you stop!??" I screamed at her.

"I'm sorry Craig. I'm so turned on. You've caught us now; you might as well let us finish. Fuck, this dick is huge!" My sister admired my girlfriend's dick and smothered the head with kisses.

"Your brother's is bigger." Michelle laughed.

"What!???" My sister turned her head to look at me. "Are you serious!? You're bigger than this!???" She was amazed.

"Yeah, come on baby. Why don't you prove it? Take your cock out for your big sister." Michelle said to me. I don't know what came over me in that moment. Maybe it was the sheer anger at both of them but I unzipped my pants and took out my cock and showed it to her.

"Woah, Craig! What the fuck! I'm your sister! Why are you showing me your dick!??" She was stunned.

"Because I love Michelle and I don't wanna lose her. I can't stand the thought of my sister being the reason for our relationship ending. Seems like the only way to get through this is to get involved as Michelle said. Besides, Michelle gives the best blowjobs I've ever had; and if she is saying that you give great head, then you must be incredible at sucking cock."

"Woah, little brother. This is too far!" Kim retorted.

"You think I'm little, sis?" I was openly stroking my cock Infront of my sister.

"No, your dick is really big. I think it might just be bigger than Michelle's, but I'm not sucking your cock!" My sister insisted.